WO2001004409A1 - Dyeing process with sulfur dyes - Google Patents
Dyeing process with sulfur dyes Download PDFInfo
- Publication number
- WO2001004409A1 WO2001004409A1 PCT/IB2000/000937 IB0000937W WO0104409A1 WO 2001004409 A1 WO2001004409 A1 WO 2001004409A1 IB 0000937 W IB0000937 W IB 0000937W WO 0104409 A1 WO0104409 A1 WO 0104409A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sulfur
- dyeing
- process according
- polyamide
- substrate
- Prior art date
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/30—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using sulfur dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/243—Polyamides; Polyurethanes using vat or sulfur dyes, indigo
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8209—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing amide groups
Definitions
- This invention comprises a process for dyeing polyamide substrates or polyamide-containing substrates with sulfur dyes and substrates dyed with such a dye.
- Sulfur dyes are an important class of dyes. This class is extensively described in Venkatamaran "The Chemistry of Synthetic Dyes", volume II (chapters XXXV and XXXVI) (1952) and volume VII (1974) and in the Colour Index. Essentially they are dyes which contain aromatically attached oligo sulfur linkages which are reducible to thiol groups and which may be of oligomeric or polymeric structure. They are mainly obtained by thionation of the respective intermediates at high temperature, for example above 100°C, especially in the temperature range from 1 10 to 300°C (eg by baking or in the melt or in the presence of water and/or an inert organic solvent).
- Sulfur dyes are most prominently used in cellulose dyeing.
- the most widely used sulfur dye of this category is C.I. Sulfur Black 1 , which is based on the organic compound I.
- sulfur dyes include CI. Sulfur Black 2, CI. Sulfur Black 1 1 , CI. Sulfur Black 18, CI. Sulfur Green 35, etc. A detailed list may be found in the Colour Index.
- sulfur dyes are used in particular to dye cellulose or cellulose- containing fabric.
- the most widely used process for dyeing these materials is the exhaust and continuous process.
- Sulfur dyes are preferably used in aqueous form, especially in the form of an aqueous paste.
- the aqueous form may be prepared, for example, by suspending a commercially available sulfur dye, or a sulfur dye prepared by baking or in the melt, in water.
- Sulfur dyes are applied to the substrates in the reduced (leuco) form and are then oxidized. That is, sulfur dyes may be added to the dyeing liquor in the reduced form or in the oxidized form, which is then reduced using a suitable reducing agent.
- Useful reducing agents are .all reducing agents known as suitable in the prior art, especially sodium hydrosulfide, sodium formaldehydesulfoxylate, potassium formaldehydesulfoxylate, zinc formaldehydesulfoxylate, thiourea, polysulfides (Na x S y ), sodium sulfide, hydroxyacetone and glucose.
- Useful oxidizing agents include all oxidizing agents known as suitable in the prior art, especially bichromates (K 2 Cr0 7 . Na 2 CrO ), bromates (NaBr0 3 , NaI0 3 ), bromites (NaBr0 2 ), perborates ( aB0 3 ), persulfates ( 2 S 2 0 8 , Na 2 S 2 O 8 ), hydrogen peroxide and chlorates (NaClO 3 ).
- Polyamide substrates and polyamide-containing substrates have hitherto not been satisfactorily dyeable with certain sulfur dyes, for example C.I. Sulfur Black 1 or CI. Sulfur Black 2.
- sulfur dyes for example C.I. Sulfur Black 1 or CI. Sulfur Black 2.
- polyamide/cotton blends were not dyeable on-tone with just one dye.
- polyamide substrates or polyamide-containing substrates for example polyamide/Lycra ® , polyamide/cotton, polyamide/cotton/Lycra ® (Lycra ® is a trademark of DuPont), polyamide/cotton, etc, to be dyed with Sulfur Black 1, Sulfur Black 2 or Sulfur Green 16 in good fastnesses.
- Polyamide microfibers for example Meryl ® (Meryl ® is a trademark of Nylstar) are likewise suitable for dyeing according to the invention.
- a further advantage of the process according to the invention is that good on-tone dyeing is obtained with just one dye and a one-step dyeing process, for example on a cotton/polyamide substrate, and this is something previously known processes did not provide.
- polyamides and polyamide-containing substrates are dyed with individual sulfur dyes at up to 95°C and a pH of 12 - 14.
- the sulfur dyes used may be used not only in reduced form but also in oxidized form.
- the process of the invention is particularly suitably carried out using dyes of the Diresul ® EV type.
- Diresul ® is a trademark of Clariant.
- the liquor ratio used in the examples hereinbelow is always 10: 1 , unless otherwise stated.
- the substrate has very good fastnesses.
- the aqueous dyeing liquor is made up of 15% of Diresul ® Black EV-4G (C.I. Sulfur Black 1 )
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the aqueous dyeing liquor is made up of 15% of Diresul ® Black EV-4G (C.I. Sulfur Black 1 ) (manufactured by Clariant), 3 g/1 of calcined sodium carbonate, l ml/1 of a wetting agent and 5g/l of sodium formaldehydesulfoxylate.
- the polyamide substrate (PA 6.6 Nylsuisse Art.2044) is introduced into the dyeing liquor at 60°C.
- the dyeing liquor is then heated to 95°C at 2°C/min. Dyeing continues at 95°C for 60 minutes, and the bath is then cooled down to 70°C at 2°C/min.
- the pH is between 9 and 10.5 during the dyeing process.
- the substrate is then rinsed with hot and cold water.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate has good fastnesses.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate has good fastnesses.
- the aqueous dyeing liquor is made up of 15% of Diresul ® Olive RDT-B liq. (C.I. Sulfur Green 16) (manufactured by Clariant), 3 g/1 of calcined sodium carbonate, lml/1 of a wetting agent and 5g/l of sodium formaldehydesulfoxylate.
- the polyamide substrate (PA 6.6 Nylsuisse Art.2044) is introduced into the dyeing liquor at 60°C
- the dyeing liquor is then heated to 95°C at 2°C/min.
- Dyeing continues at 95°C for 60 minutes, and the bath is then cooled down to 70°C at 2°C/min.
- the pH is between 9 and 10.5 during the dyeing process.
- the substrate is then rinsed with hot and cold water.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate has good fastnesses.
- the aqueous dyeing liquor is made up of 20% of Diresul ® Black EV-PL (C.I. Sulfur Black 2) (manufactured by Clariant), 3g/l of calcined sodium carbonate, 1 ml/1 of a wetting agent and introduced into the dyeing liquor at 60°C The dyeing liquor is then heated to 1 10°C at
- the pH is between 9 and 10.5 during the dyeing process.
- the substrate is then rinsed with hot and cold water.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate has good fastnesses.
- the aqueous dyeing liquor is made up of 15% of Diresul ® Black EV-4G (C.I. Sulfur Black 1 ) (manufactured by Clariant), 3g/l of calcined sodium carbonate, lml/1 of a wetting agent and 5g/l of sodium formaldehydesulfoxylate.
- the polyamide/Lycra (80:20) blend substrate is introduced into the dyeing liquor at 60°C
- the dyeing liquor is then heated to 95°C at 2°C/min.
- Dyeing continues at 95°C for 60 minutes, and the bath is then cooled down to 70°C at 2°C/min.
- the pH is between 9 and 10.5 during the dyeing process.
- the substrate is then rinsed with hot and cold water.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate has good fastnesses.
- the aqueous dyeing liquor is made up of 15% of Diresul ® Black EV-4G (C.I. Sulfur Black 1 ) (manufactured by Clariant), 20g l of calcined Glauber salt, 3g/l of calcined sodium carbonate, lml/1 of a wetting agent and 5g/l of sodium formaldehydesulfoxylate.
- the polyamide/cotton/Lycra (30:60: 10) blend substrate is introduced into the dyeing liquor at 60°C
- the dyeing liquor is then heated to 95°C at 2°C/min. Dyeing continues at 95°C for 60 minutes, and the bath is then cooled down to 70°C at 2°C/min.
- the pH is between 9 and 10.5 during the dyeing process.
- the substrate is then rinsed with hot and cold water.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate shows excellent equalization in color strength and hue between the cotton and the polyamide and has commercially acceptable fastnesses.
- the aqueous dyeing liquor is made up of 15% of Diresul ® Black EV-4G (CI. Sulfur Black 1 ) (manufactured by Clariant), 20g/l of calcined Glauber salt, 3g/l of calcined sodium carbonate, lml/1 of a wetting agent and 5 g/1 of sodium formaldehydesulfoxylate.
- the polyamide/cotton Lycra ® (30:60: 10) blend substrate is introduced into the dyeing liquor at 60°C
- the dyeing liquor is then heated to 1 10°C at 2°C/min. Dyeing continues at 1 10°C for 60 minutes, and the bath is then cooled down to 70°C at 2°C/min.
- the pH is between 9 and 10.5 during the dyeing process.
- the substrate is then rinsed with hot and cold water.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate shows excellent equalization in color strength and hue between the cotton and the polyamide and has commercially acceptable fastnesses.
- the aqueous dyeing liquor is made up of 15% of Diresul ® Black EV-4G (C.I. Sulfur Black 1 ) (manufactured by Clariant), 3g/l of calcined sodium carbonate, l ml/1 of a wetting agent and 5 g/1 of sodium formaldehydesulfoxylate.
- the polyamide/Lycra ® (80:20) blend substrate is introduced into the dyeing liquor at 60°C
- the dyeing liquor is then heated to 95°C at 2°C/min.
- Dyeing continues at 95°C for 60 minutes, and the bath is then cooled down to 70°C at 2°C/min.
- the pH is between 9 and 10.5 during the dyeing process.
- the substrate is then rinsed with hot and cold water.
- the dye is oxidized on the substrate by using a sodium bromate solution (4g/l) at 70°C and a pH of 3 - 4, adjusted with acetic acid, for 30 minutes.
- the substrate is then rinsed with hot and cold water.
- the substrate has good fastnesses.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00939011A EP1200669A1 (en) | 1999-07-12 | 2000-07-11 | Dyeing process with sulfur dyes |
KR1020027000331A KR20020027484A (en) | 1999-07-12 | 2000-07-11 | Dyeing process with sulfur dyes |
MXPA02000423A MXPA02000423A (en) | 1999-07-12 | 2000-07-11 | Dyeing process with sulfur dyes. |
JP2001509800A JP2003504532A (en) | 1999-07-12 | 2000-07-11 | Coloring method with sulfur dye |
BR0012389-7A BR0012389A (en) | 1999-07-12 | 2000-07-11 | Sulfur dyeing process |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1278/99 | 1999-07-12 | ||
CH127899 | 1999-07-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001004409A1 true WO2001004409A1 (en) | 2001-01-18 |
Family
ID=4206683
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2000/000937 WO2001004409A1 (en) | 1999-07-12 | 2000-07-11 | Dyeing process with sulfur dyes |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1200669A1 (en) |
JP (1) | JP2003504532A (en) |
KR (1) | KR20020027484A (en) |
BR (1) | BR0012389A (en) |
MX (1) | MXPA02000423A (en) |
WO (1) | WO2001004409A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108797155A (en) * | 2018-05-16 | 2018-11-13 | 佛山大唐纺织印染服装面料有限公司 | It is a kind of have wash the whole dyeing technique for taking off style coating denim fabric |
EP3536737A1 (en) * | 2018-03-08 | 2019-09-11 | Archroma IP GmbH | Method for dyeing a plastic object |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR906232A (en) * | 1944-08-02 | 1945-12-27 | Ig Farbenindustrie Ag | Process for dyeing polyamides and polyurethanes using sulfur dyes |
DE818041C (en) * | 1948-03-04 | 1951-10-22 | Johann Maria Lanczer | Process for dyeing synthetic polyamide and polyester fibers and fabrics made from these fibers |
US2904385A (en) * | 1956-07-17 | 1959-09-15 | Oreal | Dyeing animal fibres and compositions therefor |
FR2250848A1 (en) * | 1973-11-13 | 1975-06-06 | Cassella Farbwerke Mainkur Ag |
-
2000
- 2000-07-11 WO PCT/IB2000/000937 patent/WO2001004409A1/en not_active Application Discontinuation
- 2000-07-11 EP EP00939011A patent/EP1200669A1/en not_active Withdrawn
- 2000-07-11 JP JP2001509800A patent/JP2003504532A/en active Pending
- 2000-07-11 MX MXPA02000423A patent/MXPA02000423A/en not_active Application Discontinuation
- 2000-07-11 KR KR1020027000331A patent/KR20020027484A/en not_active Application Discontinuation
- 2000-07-11 BR BR0012389-7A patent/BR0012389A/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR906232A (en) * | 1944-08-02 | 1945-12-27 | Ig Farbenindustrie Ag | Process for dyeing polyamides and polyurethanes using sulfur dyes |
DE818041C (en) * | 1948-03-04 | 1951-10-22 | Johann Maria Lanczer | Process for dyeing synthetic polyamide and polyester fibers and fabrics made from these fibers |
US2904385A (en) * | 1956-07-17 | 1959-09-15 | Oreal | Dyeing animal fibres and compositions therefor |
FR2250848A1 (en) * | 1973-11-13 | 1975-06-06 | Cassella Farbwerke Mainkur Ag |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3536737A1 (en) * | 2018-03-08 | 2019-09-11 | Archroma IP GmbH | Method for dyeing a plastic object |
CN108797155A (en) * | 2018-05-16 | 2018-11-13 | 佛山大唐纺织印染服装面料有限公司 | It is a kind of have wash the whole dyeing technique for taking off style coating denim fabric |
Also Published As
Publication number | Publication date |
---|---|
BR0012389A (en) | 2002-03-19 |
MXPA02000423A (en) | 2002-07-30 |
EP1200669A1 (en) | 2002-05-02 |
JP2003504532A (en) | 2003-02-04 |
KR20020027484A (en) | 2002-04-13 |
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